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This is a bit confusing. Yes means the proxy is enabled. No means the proxy has been disabled for that site meaning that site has been white-listed.
In general, the umbrella button and the proxy button white-lists refer to the same thing and should be in sync. There may sometimes be a lag if you've loaded the proxy whitelisting page but then change the umbrella button setting...there will be a mismatch until you refresh the whitelisting page.
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